I've checked my Hyper-V settings and PowerShell Module is enabled. I've also found this documented issue: https://github.com/docker/machine/issues/4342 but it is not the same issue since I do not have VMware PowerCLI installed. The issue was closed with a push to the repo and is supposedly fixed in 0.14.0-rc1, build e918c74 so I tried it anyways. After replacing my docker-machine.exe, I'm still getting the error and still getting the error even if I reinstall Docker for Windows.
For some more background, this error starting happening after a reinstall because my Docker install had an error: https://github.com/docker/for-win/issues/1691, however, I'm not longer getting that issue after reinstalling.
For those who struggle with this issue in Windows, Follow the instruction here